You can achieve that with the Templater plugin.
This is using the current macOS. Other OS may differ, as the plugin relies on the system command line.
- Create a user function (eg.
question)
file="Path/To/Your/Questions File.txt"
size=$(wc -l < $file)
line=$((1 + $RANDOM % $size))
echo $(sed -n "$line"p < $file)
- Use that function in your desired template. For example:
# Daily
## Daily Questions
### 1. <% tp.user.question() %>
---
### 2. <% tp.user.question() %>
---
### 3. <% tp.user.question() %>
---
### 4. <% tp.user.question() %>
---
### 5. <% tp.user.question() %>